Water → HCID 18430857, compound

Participants

Reaction Steps

To a solution of l-[(4-benzyl-1-piperazinyl)methyl]ethanecarbonitrile (9.0 g/39.3 mmol) in tetrahydrofuran (300 ml) was added dropwise 2.0 M solution of lithium diisopropylamide (98 ml/197 mmol) at −78° C., and then the resulting mixture was stirred for 30 minutes. 1,5-Dibromopentane (8 ml/59 mmol) was added to the mixture in one portion and the resulting mixture was allowed to warm to ambient temperature. The mixture was stirred for 3 hours. Then, H2O (150 ml) was added for quenching. The mixture was extracted with ethyl acetate (200 ml×2). The combined extracts were washed with brine (50 ml), dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (Si, 230-400 mesh/150 g/dichloromethane:methanol=100:0-100:4) to give a brown solid (11 g/94%).

Provenance & Evidence